Isolation and bacterial expression of a sesquiterpene...

Details Isolation and bacterial expression of a sesquiterpene... Isolation and bacterial expression of a sesquiterpene...

1999-07-27

2001-07-10

Prouty, Rebecca E. (Department: 1652)

Chemistry: molecular biology and microbiology

Plant cell or cell line, per se ; composition thereof;...

Plant cell or cell line, per se, contains exogenous or...

C435S183000, C435S320100, C435S252300, C435S252100, C536S023100, C536S023200

Reexamination Certificate

active

06258602

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to nucleic acid sequences which code for (E)-&bgr;-farnesene synthases, such as the (E)-&bgr;-farnesene synthase from
Mentha piperita
, and to vectors containing the sequences, host cells containing the sequences and methods of producing recombinant (E)-&bgr;-farnesene synthases and their mutants.
BACKGROUND OF THE INVENTION
(E)-&bgr;-farnesene (
FIG. 1
) is an acyclic sesquiteipene olefin that occurs in a wide range of both plant and animal taxa. Over 600 papers have been published on the occurrence of this natural product and its deployment as an important courier in chemical communication. The olefin is found in the essential oil of hundreds of species of both gymnosperms, such as
Torreya taxifolia
(Florida torreya) (Shu, C. K., Lawrence, B. M. and Croom, E. M., Jr. (1995)
J. Essent Oil Res.
7, 71-72) and
Larix leptolepis
(larch) (Nabeta, K., Ara, Y., Aoki, Y. and Miyake, M. (1990)
J. Nat. Prod.
53, 1241-1248), and angiosperms, such as
Robinia pseudoacacia
(black locust) (Kamden, D. P., Gruber, K., Barkman, L. and Gage, D. A. (1994)
J. Essent. Oil Res.
6, 199-200),
Medicago sativa
(alfalfa) (Kamm, J. A. and Buttery. R. G. (1983)
Entomol. Exp. Appl.
33, 129-134),
Chamomilla recutita
(chamomile) (Matos. P. J. A., Machiado, M. I. L., Alencar, J. W. and Craveiro, A. A. (1993)
J. Essent. Oil Res.
5, 337-339),
Vitis vinifera
(grapes) (Buchbauer, G., Jirovetz, L., Wasicky, M. and Nikiforov, A. (1994)
J. Essent. Oil Res.
6, 311-314),
Cannabis sativa
(hemp) (Lemberkovics, E., Veszki, P., Verzar-Petri, G. and Trka, A. (1981)
Sci. Pharm.
49, 401-408),
Zea mays
(corn) (Turlings, T. C. J., Tumlinson, J. H., Heath, R. R., Proveaux, A. T. and Doolittle, R. E. (1991)
J. Chem. Ecol.
17, 2235-2251),
Piper nigruim
(black pepper),
Daucus carota
(carrot), and
Mentha x piperita
(peppermint) (Lawrence, B. M. (1972)
Ann. Acad. Bras. Cienc.
44, (suppl.), 191-197).
While socially dominant male mice produce both &agr;-farnesene and (E)-&bgr;-farnesene in their urine as pheromones (Novotny, M., Harvey, S. and Jemiolo, B. (1990)
Experientia
46, 109-113), it is in the insects and plants that the use of (E)-&bgr;-farnesene as a semiochemical is most extensive. (E)-&bgr;-Farnesene is emitted by the Dufour's gland of andrenid bees (Fernandes, A., Duffield, R. M., Wheeler, J. W. and LaBerge, W. E. (1981)
J. Chem. Ecol.
7, 453-460) and by several genera of ants (Ali, M. F., Morgan, E. D., Attygalle, A. B. and Billen, J. P. J. (1987)
Z. Naturforsch.
42, 955-960; Jackson, B. D., Morgan, E. D. and Billen, J. P. J. (1990)
Naturwiss.
77, 187-188; Ollet, D. G., Morgan, E. D., Attygalle, A. B. and Billen. J. P. J. (1987)
Z. Naturforsch.
42, 141-146), where it serves both as a defensive allomone and as a trail pheromone. This sesquiterpene is synthesized de novo in the osmetrial glands of larval Papilio (Lepidoptera:Papilionidae) as an allomone (Honda, K. (1990)
Insect Biochem.
20, 245-250), and it functions as a feeding stimulant to the sand fly
Lutzomyia longipalpis
(Diptera:Psychodidae), an important vector of the blood disease leishmaniasis (Tesh, R. B., Guzman, H. and Wilson, M. (1992)
J. Med. Entomol.
29, 226-231). Several species of predatory carabid beetles use E-&bgr;-farnesene as a prey-finding kairomone (Kielty, J. P., Allen-Williams, L. J., Underwood, N. and Eastwood, E. A. (1996)
J. Insect Behav.
9, 237-250). When released by corn, this olefin is also a kairomonal oviposition stimulant to the European corn borer (Ostrinia) (Binder, B. F., Robbins, J. C. and Wilson., R. L. (1995)
J. Chem. Ecol.
21, 1315-1327). (E)-&bgr;-farnesene is the major component of pollen odor in Lupinus and stimulates pollination behavior in bumblebees (Dobson, H. E. M., Groth, I. and Bergstroem, G. (1996)
Am. J. Bot.
83, 877-885). Feeding by larval lepidopterans, such as Heliothis or Spodoptera (Noctuidae), increases the amount of (E)-&bgr;-farnesene released by corn; the volatile olefin is then detected as a synomone by the parasitic wasp
Cotesia marginiventris
(Hymenoptera:Braconidae) for locating the lepidopteran hosts (Turlings, T. C. J., Tumlinson, J. H., Heath, R. R., Proveaux, A. T. and Doolittle, R. E. (1991)
J. Chem. Ecol.
17, 2235-2251). Circumstantial evidence also suggests the lepidopteran induced production and emission of (E)-&bgr;-farnesene from corn serves as a synomone for
Cotesia kariyai
(Takabayashi, J., Takahashi, S., Dicke, M. and Posthumnus, M. A. (1995)
J. Chem. Ecol.
21, 273-287) and from cotton leaves as a synomone for
C. marginiventris
(Pare, P. W. and Tumlinson, J. H. (1997)
Nature
385, 30-31; Loughrin, J. H., Manukian, A., Heath, R. R., Turlings, T. C. J. and Turnlinson, J. H. (1994)
Proc. Natl. Acad. Sci. USA
91, 11836-11840).
Perhaps of greatest significance in plant-insect interactions is the use of E-&bgr;-farnesene by most aphid species as an alarm pheromone (Bowers, W. S., Nault, L. R., Webb, R. E. and Dutky, S. R. (1972)
Science
177. 1121-1122; Edwards, L. J., Siddall, J. B., Dunham, L. L., Uden, P. and Kislow, C. J. (1973)
Nature
241. 126-127). Aphids exposed to (E)-&bgr;-farnesene become agitated and disperse from their host plant (Wohlers, P. (1981)
Z. Angew. Entomol.
92, 329-336). Alate aphids are usually more sensitive than are apterae species and will often not colonize a host displaying (E)-&bgr;-farnesene. Ants that defend aphids are sensitive to host-emitted (E)-&bgr;farnesene and, when exposed, will display aggressive behavior (Nault, L. R. and Montgomery, M. E. (1976)
Science
192, 1349-1351). (E)-&bgr;-farnesene also mimics the action of juvenile hormone III in some insects (Mauchamp, B. and Pickett. J. J. (1987)
Agronomie
7, 523-529), may play a role in control of aphid morphological types, and is acutely toxic to aphids at a dose of 100 ng/aphid (van Oosten, A. M., Gut, J., Harrewijn, P. and Piron, P. G. M. (1990)
Acta Phytopathol. Enlomol. Hung.
25, 331-342). (E)-&bgr;-farnesene vapor is also toxic to whiteflies (Klijnstra, K. W., Corts, K. A. and van Oosten, A. M. (1992)
Meded. Fac. Landbouwwet.
57, 485-491).
Efforts to control aphid behavior by topical application of (E)-&bgr;-farnesene to crops have met with little success, due to volatility and rapid oxidative inactivation in air (Dawson, G. W., Griffiths, D. C., Pickett. J. A., Plumb, R. T., Woodcock, C. M. and Zhang, Z. N. (1988)
Pest. Sci.
22, 17-30). Derivatives of (E)-&bgr;-farnesene with reduced volatility, or increased stability, have shown promise in reducing aphid-transmitted viruses, such as barley mosaic virus (Dawson, G. W., Griffiths, D. C., Pickett, J. A., Plumb, R. T., Woodcock, C. M. and Zhang, Z. N. (1988)
Pest. Sci.
22, 17-30), potato virus Y (Gibson, R. W., Pickett, J. A., Dawson, G. W., Rice. A. D. and Stribley, M. F. (1984)
Ann. Appl. Entomol.
104, 203-209), and beet mosaic virus (Gibson, R. W., Pickett, J. A., Dawson, G. W., Rice, A. D. and Stribley, M. F. (1984)
Ann. Appl. Entomol.
104, 203-209). The wild potato
Solanum berthaultii,
which produces (E)-&bgr;-farnesene in type A trichomes, is more repellent to the green peach aphid than are commercial varieties of
S. tuberosum
that produce lower levels of the olefin (Gibson, R. W. and Pickett, J. A. (1983)
Nature
302, 608-609; Ave, D. A., Gregory, P. and Tingey, W. M. (1987)
Entomol. Exp. App.
44, 131-138). In alfalfa. repellency to the blue alfalfa aphid and the pea aphid is correlated with the leaf content of (E)-&bgr;-farnesene, but not with the amount of the co-occurring sesquiterpene caryophyllene (Mostafavi, R., Henning, J. A., Gardea-Torresday, J. and Ray. I. M. (1996)
J. Chem. Ecol.
22, 1629-1638).
For plants that produce (E)-&bgr;-farnesene, breeding for increased production has met with some success (Mostafavi, R., Henning, J. A., Gardea-Torresday, J. and Ray, I. M. (1996)
J. Chem. Ecol.
22, 1629-1638), but has been limited by genetic variation in these species. (E)-&bgr;-farnesene synthase has been purified from maritime pine (
Pinus pinaster
) and characterized (Salin, F., Paul

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